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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Compare 430 Condo Rentals in Waynesboro with updated reviews, rates, and availability.

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

9.0 out of 10, Wonderful, (270)
"We really appreciate the cleanliness and location of this property! We had a great stay and look forward to returning! Ps love the art!! "
The price is $241
includes taxes & fees
$215 per night
May 5 - May 6
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

10.0 out of 10, Exceptional, (312)
"Love this condo! Has a fireplace, upstairs and view of the falling snow!"
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly
Pool

New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly

9.6 out of 10, Exceptional, (124)
"This property is one of the best prperties we have ever stayed at. The owner is very responsive and goes the extra mile. We will definitely rent this property again!!"
The price is $246
includes taxes & fees
$219 per night
May 4 - May 5
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly
WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS
Interior

WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS

10.0 out of 10, Exceptional, (62)
"The property was well maintained with exceptional views. We enjoyed our stay from start to finish and never grew tired of the property or the mountain views."
WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS
Wintergreen Condo -Steps to Ski and restaurants
Terrace/patio

Wintergreen Condo -Steps to Ski and restaurants

9.8 out of 10, Exceptional, (16)
"Excellent location."
The price is $261
includes taxes & fees
$232 per night
May 1 - May 2
Wintergreen Condo -Steps to Ski and restaurants
Dobie condo, renovated top to bottom! LOTS OF DETAILED INFO LISTED ☺️
Property grounds

Dobie condo, renovated top to bottom! LOTS OF DETAILED INFO LISTED ☺️

10.0 out of 10, Exceptional, (170)
"We had another great stay at this property and already rebooked for next year!"
Dobie condo, renovated top to bottom! LOTS OF DETAILED INFO LISTED ☺️
Premiere Two bedroom getaway Slope Side Wintergreen Resort Condo
Smart TV, fireplace, books

Premiere Two bedroom getaway Slope Side Wintergreen Resort Condo

10.0 out of 10, Exceptional, (4)
"We have stayed here several times and love it! Great updated property and with fully equipped kitchen. The owners are very easy to work with, and the location is perfect for ski in/ski out with minimal stairs. "
Premiere Two bedroom getaway Slope Side Wintergreen Resort Condo
Endless Mountain Top Views from All The Way Up!
Property grounds

Endless Mountain Top Views from All The Way Up!

10.0 out of 10, Exceptional, (70)
"The property was great and exactly as advertised. I’ve stayed at four places around Wintergreen, and this was definitely the best. The communication and responsiveness from the hosts was perfect."
The price is $317
includes taxes & fees
$282 per night
May 4 - May 5
Endless Mountain Top Views from All The Way Up!
View from the Top
Property grounds

View from the Top

10.0 out of 10, Exceptional, (54)
"Great quick stay in a lovely area with an amazing view"
View from the Top
Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!
Miscellaneous

Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!

10.0 out of 10, Exceptional, (234)
"Maureen was incredibly kind and helpful through out our stay. The place is beautifully decorated with amazing views! Our family had a wonderful stay together! We will definetly look to stay here again! "
Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!
Wintergreen. Sunset Vista Villa - Sea of Mountains
Interior

Wintergreen. Sunset Vista Villa - Sea of Mountains

10.0 out of 10, Exceptional, (68)
"Great location and property"
The price is $279
includes taxes & fees
$248 per night
May 5 - May 6
Wintergreen. Sunset Vista Villa - Sea of Mountains
Travelers' Rest--Your Wintergreen Retreat in the Center of it All!
Outdoor dining

Travelers' Rest--Your Wintergreen Retreat in the Center of it All!

9.6 out of 10, Exceptional, (26)
"Great place to stay, would book again!"
Travelers' Rest--Your Wintergreen Retreat in the Center of it All!
Walk to Market/Private community outdoor pool!
Fridge, microwave, oven, stovetop

Walk to Market/Private community outdoor pool!

9.6 out of 10, Exceptional, (67)
"Nice condo, near all the Wintergreen activities."
Walk to Market/Private community outdoor pool!
Walk to Lifts: Wintergreen Resort Condo
Exterior

Walk to Lifts: Wintergreen Resort Condo

7.6 out of 10, Good, (5)
"Everything was clean, everything we needed for our stay! Was to slopes, walk to the market, close to everything! We love laurelwoods! "
Walk to Lifts: Wintergreen Resort Condo
Top of Mountain 2 BR Condo, Short Walk to Highlands Ski Lift and Scenic Views
Miscellaneous

Top of Mountain 2 BR Condo, Short Walk to Highlands Ski Lift and Scenic Views

9.8 out of 10, Exceptional, (46)
"Great family getaway. While it rained and conditions were terrible for snowboarding/skiing, we had everything we needed to be comfortable while staying at this condo! "
Top of Mountain 2 BR Condo, Short Walk to Highlands Ski Lift and Scenic Views
Wintergreen Resort Vacation Rental w/ Pool Access!
Property grounds

Wintergreen Resort Vacation Rental w/ Pool Access!

10.0 out of 10, Exceptional, (16)
"Really worked well for our family "
Wintergreen Resort Vacation Rental w/ Pool Access!
Water Street Condo | Overlooking Downtown
Smart TV

Water Street Condo | Overlooking Downtown

8.4 out of 10, Very Good, (31)
"We all had so much fun and plan to come back again!"
Water Street Condo | Overlooking Downtown
Newly Updated Cozy Condo in the Heart of Wintergreen! Pet friendly.
Property grounds

Newly Updated Cozy Condo in the Heart of Wintergreen! Pet friendly.

10.0 out of 10, Exceptional, (141)
"This was our second stay here. Perfect for a couple! Great location in the mountain right near the general store and main lodge. "
Newly Updated Cozy Condo in the Heart of Wintergreen! Pet friendly.
Best Panoramic Views with 2 Floors
TV, fireplace, books

Best Panoramic Views with 2 Floors

10.0 out of 10, Exceptional, (65)
"We loved the condo .I've stayed in many different condo complexes at Wintergreen (i've also owned a couple) and this is definitely near the top of my list along with being on top of the mountain.Beautiful view!!"
The price is $387
includes taxes & fees
$346 per night
May 1 - May 2
Best Panoramic Views with 2 Floors
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Miscellaneous

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

9.4 out of 10, Exceptional, (10)
"I was at a conference at Wintergreen and this was the perfect location. The area is beautiful! The condo was clean and well-equipped. "
The price is $220
includes taxes & fees
$196 per night
May 1 - May 2
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Waynesboro

Charming 5 Bedroom Historic brick home w/ sprawling river views, pool & hot tub!
Outdoor pool

Charming 5 Bedroom Historic brick home w/ sprawling river views, pool & hot tub!

10.0 out of 10, Exceptional, (6)
"We really enjoyed our stay at the property! With so many rooms, there was space for everyone, and everything was very clean upon our arrival. The hot tub was perfect for a cold night! "
The price is $519
includes taxes & fees
$466 per night
May 1 - May 2
Charming 5 Bedroom Historic brick home w/ sprawling river views, pool & hot tub!
Massanutten's Woodstone Meadows by Tripforth
Outdoor pool

Massanutten's Woodstone Meadows by Tripforth

4.0 star property
9.0 out of 10, Wonderful, (212)
"Nice and quiet place to stay over the weekend and food was great "
Massanutten's Woodstone Meadows by Tripforth
Mountainside Villas at Massanutten by Tripforth
Indoor pool, outdoor pool

Mountainside Villas at Massanutten by Tripforth

3.5 star property
9.0 out of 10, Wonderful, (303)
"Nice stay in the midst of "
Mountainside Villas at Massanutten by Tripforth
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

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What is there to do in Waynesboro near my condo?
You’ll find plenty of awesome things to sink your teeth into in Waynesboro. Check out leading attractions like Wayne Theatre, Basic City Beer Co. and P. Buckley Moss Gallery. Hermitage Hill Farm & Stables, Rockfish Gap Entrance Shenandoah and Zeus Digital Theater are also on many to-do lists.